Hotels in Chestertown
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Top Rated Chestertown Hotels
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd Chestertown MD
Free Cancellation
7.76 mi from city center
$124 nightly
The price is $137 total per night
$137 total
Sep 10 - Sep 11
Total with taxes and fees
Guests staying at The Lodge at Great Oak Landing enjoy access to a golf course, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. Other amenities at this beach lodge include a seasonal outdoor pool, coffee/tea in a common area, and laundry facilities.
Pool
Parking included
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
$72 nightly
The price is $80 total per night
$80 total
Sep 15 - Sep 16
Total with taxes and fees
Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a vending machine, and a TV in a common area.
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
Free Cancellation
Reserve now, pay when you stay
0.64 mi from city center
$104 nightly
The price is $115 total per night
$115 total
Oct 4 - Oct 5
Total with taxes and fees
Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
Historic Inns of Annapolis
58 State Circle Annapolis MD
Free Cancellation
Reserve now, pay when you stay
27.98 mi from city center
$147 nightly
The price is $168 total per night
$168 total
Sep 28 - Sep 29
Total with taxes and fees
At Historic Inns of Annapolis, guests have access to a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is available for USD 50.00 per night, and there's also limo/town car service. The front desk has multilingual staff on hand 24/7 to help with securing valuables, luggage storage, and tours or tickets. Other amenities at this historic hotel include conference space, coffee/tea in a common area, and express check-in.
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
Free Cancellation
Reserve now, pay when you stay
24.05 mi from city center
$74 nightly
The price is $85 total per night
$85 total
Sep 15 - Sep 16
Total with taxes and fees
Guests of La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh enjoy a gym, free WiFi in public areas, and a business center. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to assist with concierge services and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
Breakfast included
Pet friendly
Pendry Baltimore
1715 Thames St. Baltimore MD
Free Cancellation
Reserve now, pay when you stay
28.3 mi from city center
$427 nightly
The price is $502 total per night
$502 total
Sep 28 - Sep 29
Total with taxes and fees
Guests of Pendry Baltimore enjoy a 24-hour gym, free WiFi in public areas, and meeting rooms. Valet parking is USD 65 per night if you plan to drive, or hop aboard the airport shuttle (available 24 hours) for USD 108.39 per vehicle one-way. The 24-hour front desk has staff standing by to help with concierge services, dry cleaning/laundry, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a business center, a seasonal outdoor pool, and a terrace.
Hampton Inn Baltimore/Glen Burnie
6617 Ritchie Hwy Glen Burnie MD
Free Cancellation
Reserve now, pay when you stay
29.11 mi from city center
$112 nightly
The price is $127 total per night
$127 total
Sep 20 - Sep 21
Total with taxes and fees
Guests of Hampton Inn Baltimore/Glen Burnie enjoy access to free WiFi in public areas, conference space, and a 24-hour business center. If you plan to drive, free parking is available. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, securing valuables, and luggage storage. Additional amenities include coffee/tea in a common area, express check-out, and a water dispenser.
Breakfast included
Pet friendly
Best Western Plus Hotel & Conference Center
5625 O'Donnell Street Baltimore MD
Free Cancellation
Reserve now, pay when you stay
25.92 mi from city center
$116 nightly
The price is $131 total per night
$131 total
Sep 15 - Sep 16
Total with taxes and fees
Guests of Best Western Plus Hotel & Conference Center have access to an indoor pool, a gym, and free WiFi in public areas. There's free parking and a cruise ship terminal shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and a conference center.
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
27.93 mi from city center
$231 nightly
The price is $264 total per night
$264 total
Oct 4 - Oct 5
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection offers a 24-hour gym, a rooftop terrace, and free WiFi in public areas. Valet parking is available for USD 39 per day. The 24-hour front desk has staff standing by to help with securing valuables, concierge services, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include meeting rooms, conference space, and a 24-hour business center.
Hampton Inn & Suites Edgewood/Aberdeen-South
2110 Emmorton Park Rd Edgewood MD
Free Cancellation
Reserve now, pay when you stay
20.73 mi from city center
$84 nightly
The price is $95 total per night
$95 total
Sep 29 - Sep 30
Total with taxes and fees
At Hampton Inn & Suites Edgewood/Aberdeen-South, guests have access to a gym, free WiFi in public areas, and meeting rooms. Free parking is available if you drive. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, securing valuables, and dry cleaning/laundry. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Hampton Inn Baltimore/White Marsh
8225 Town Center Drive Baltimore MD
Free Cancellation
Reserve now, pay when you stay
23.47 mi from city center
$102 nightly
The price is $117 total per night
$117 total
Sep 15 - Sep 16
Total with taxes and fees
Renovated in 2023, Hampton Inn Baltimore/White Marsh offers a gym, free WiFi in public areas, and a seasonal outdoor pool. Self parking is available for USD 4.10 per day. The 24-hour front desk has staff standing by to help with luggage storage and securing valuables. Additional amenities include coffee/tea in a common area, express check-in, and express check-out.
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
2112b Emmorton Park Rd Edgewood MD
Free Cancellation
Reserve now, pay when you stay
20.67 mi from city center
$79 nightly
The price is $88 total per night
$88 total
Sep 10 - Sep 11
Total with taxes and fees
At La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A, guests have access to free WiFi in public areas, coffee in a common area, and laundry facilities. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Chestertown attractions
Cheap Chestertown hotels options
Driftwood Inn
609 Washington Avenue Chestertown MD
$64 nightly
The price is $70 total per night from Sep 10 to Sep 11
$70 total
Sep 10 - Sep 11
Total with taxes and fees
5.2/10 (181 reviews)
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
$104 nightly
The price is $115 total per night from Oct 4 to Oct 5
$115 total
Oct 4 - Oct 5
Total with taxes and fees
Where should you stay in Chestertown?
What are some of the best hotels to stay with the kids in Chestertown?
Book one of these hotels for you and the kids in Chestertown. Comfort Inn & Suites Chestertown is a hotel offering free parking, free full breakfast, and laundry facilities. You and your family can also consider Red Roof Inn & Suites Chestertown, a hotel offering free parking, laundry facilities, and free WiFi.
What are the best hotels in central Chestertown?
These are some of the most popular hotels in the center of Chestertown:
- Comfort Inn & Suites Chestertown is a hotel offering free breakfast, free WiFi, and free parking.
- Red Roof Inn & Suites Chestertown is a hotel offering free WiFi, free parking, and flat-screen TVs.
Close to central Chestertown, you'll find interesting places to visit like Chestertown Historic District.
Chestertown hotels essential information
Accommodation | 1,102 hotels |
|---|---|
Lowest Price | $70 |
Highest Price | $502 |
Popular hotels | The Lodge at Great Oak Landing, Red Roof Inn & Suites Chestertown, Comfort Inn & Suites Chestertown, Historic Inns of Annapolis, La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh, Pendry Baltimore, Hampton Inn Baltimore/Glen Burnie, Best Western Plus Hotel & Conference Center, Annapolis Waterfront Hotel, Autograph Collection, Hampton Inn & Suites Edgewood/Aberdeen-South, Hampton Inn Baltimore/White Marsh, La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A |
Recent Reviews
Historic Inns of Annapolis
5/5 Excellent
"Very convenient, right in the heart of town and near all the places that make Annapolis famous. Plus, its own bar in the basement, open five nights a week!"
A verified traveler stayed at Historic Inns of Annapolis
Posted 18 hours ago
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